Highwood, IL Homes for Sale under $800,000

Exceptional investment opportunity in the heart of downtown ! Perfectly situated on a quiet one-way street within the city's vibrant business district, this beautifully maintained and newly remodeled three-flat has been thoughtfully updated from top to bottom. Each unit showcases stylish new kitchens and baths with modern cabinetry, quartz countertops, updated lighting and fixtures, new tile,

Jim Abbott Baird & Warner

1st time on the market in nearly 100 years! Classic stucco duplex, centrally located in bustling Highwood! Each 3 bedroom two story unit offers 3 bedroom & 1.5 bathrooms with an additional 1/2 bath in each basement, along with laundry rooms and storage rooms. Beautiful hardwood floors throughout each unit (units 240 & 242). Classic 20's architecture with arches and textured plaster. Each unit has

Cory Albiani @properties Christie's International Real Estate

Custom Remodeled 5-Bedroom, 3-Bath Home - Fully Permitted Renovation! Beautifully renovated from top to bottom, this exceptional home seamlessly blends elevated finishes, thoughtful design, and functional living space. Major improvements include a new architectural shingle roof, premium LP SmartSide siding, new windows, gutters and downspouts, furnace, central A/C, water heater, updated plumbing

Dmitry Livshis Liv Realty Inc

Calling all investors & rehabbers- fabulous or opportunity for existing ranch style 2 flat in booming Highwood. Each unit is 2 beds, 1 bath, oversized garage parking and tons of storage, laundry in basement. Property is zoned as multi unit, so tear down and built opportunity available- tons of space to develop the land or improve/expand existing property.

Mada Hitchmough Compass

This stunning two-story, 2nd and 3rd floor condominium home in the heart of Fort Sheridan is one of 12 units in the historic Bakery School, offering a spacious floor plan with 2 bedrooms on the unit's main floor and a beautiful family room/ multi purpose area in the upstairs loft. The second floor entry to Unit 204 opens up to a large living room that features tall north and south facing windows,

Susan Ringel Segal @properties Christie's International Real Estate

Welcome to Highwood on the North Shore! This approximately 1,904-square-foot Lannon Stone ranch offers flexible living space, hardwood floors throughout, and two fireplaces that add warmth and character. The spacious, and light filled living room overlooks a beautiful park, while the separate dining room with rich slate flooring opens to the patio and connects to the kitchen. The house has

Carol Santi Coldwell Banker Realty

Totally updated in 2025 and move-in ready, this charming ranch blends single-level living with a fully finished basement - and serious income potential. The main level features an open kitchen with breakfast/office space, a comfortable living room, two bedrooms, and a full bath with walk-in shower, all on beautiful hardwood floors. The finished lower level adds a second full bath with tub,

Jim Abbott Baird & Warner

Rarely available, this updated and meticulously maintained first-floor ranch with a finished lower level offers an exceptional opportunity to enjoy the unique lifestyle of Fort Sheridan. Soaring ceilings and an open living and dining area create a welcoming, light-filled first impression. The inviting living room features a cozy fireplace, a spacious primary suite with a private bath, a second

Stephanie Absler-Orsi RE/MAX Top Performers

Welcome to 2648 Western Ave, an exceptional opportunity in one of Highland Park's most desirable locations. Set on a beautiful half-acre lot, this classic brick ranch with a walk-out lower level offers the perfect canvas to create your ideal home or a compelling value-add investment. With 5 bedrooms and 3.1 bathrooms, the home features a functional, flexible layout with strong bones and abundant

Aaron Walsh @properties Christie's International Real Estate

Welcome to this beautifully updated first floor, two bedroom, two bath condo in the sought after Legacy Club. Offering more than 1,700 square feet of single level living, this home combines generous space, modern comfort, and an ideal layout. Step inside to a bright, open living area featuring hardwood floors, high ceilings, and seamless access to the covered private patio, a year round extension

Carly Jones Engel & Voelkers Chicago North Shore

Charming, Updated Home in the Heart of Highland Park Welcome to this beautifully updated 4-bedroom, 2-bath home in the east Highland Park area. Located just a short walk to the vibrant downtown highwood shops and restaurants, as well as to Highwood Metra Station. The famous Morane dog park and beach is also just a skip away. This location is central to everything Highland Park has available. Not

Jeffrey Sklar Beycome Brokerage Realty LLC

Exceptional investment opportunity or owner-occupied two-flat with both units completely remodeled in 2024. Unit 1 offers 3 bedrooms and 2 full baths featuring hardwood floors, a wood-burning fireplace in the spacious living room, updated kitchen with new refrigerator, in-unit washer/dryer, and a side deck off the dining area. The finished lower level adds a family room and brand new full bath -

Jacqueline Lotzof Compass